#------------------------------------------------------------------------------ #$Date: 2015-12-18 14:49:28 +0200 (Fri, 18 Dec 2015) $ #$Revision: 171609 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/81/7118172.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7118172 loop_ _publ_author_name 'Jan Wenz' 'Christoph A. Rettenmeier' 'Hubert Wadepohl' 'Lutz H. Gade' _publ_section_title ; Catalytic C-F bond activation of geminal difluorocyclopropanes by nickel(I) complexes via a radical mechanism ; _journal_name_full Chem.Commun. _journal_page_first 202 _journal_paper_doi 10.1039/c5cc08950F _journal_volume 52 _journal_year 2016 _chemical_absolute_configuration ad _chemical_formula_moiety 'C18 H26 N3 Ni O2' _chemical_formula_sum 'C18 H26 N3 Ni O2' _chemical_formula_weight 375.13 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_block_code ga_cr6 _audit_creation_date 2015-09-25 _audit_creation_method ; Olex2 1.2 (compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998) ; _audit_update_record ; 2015-09-25 deposited with the CCDC. 2015-11-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.790(3) _cell_length_b 10.095(5) _cell_length_c 29.897(14) _cell_measurement_reflns_used 8131 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 32.19 _cell_measurement_theta_min 2.43 _cell_volume 1747.5(15) _computing_cell_refinement ; SAINT (see _computing_data_reduction). Includes estimated systematic errors of the unit cell constants from Monte Carlo simulations. ; _computing_data_collection 'SMART-5.631 (Bruker AXS, 2003)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS, 1997-2013),SADABS-2014_5 (Sheldrick and Bruker AXS, 1997-2014)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'SUPERFLIP (Palatinus, 2007-2009)' _diffrn_ambient_environment 'perfluoro polyether oil / N~2~' _diffrn_ambient_temperature 100(1) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.19 _diffrn_detector_type CCD-PXL-KAF2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method '\f- and \w-scans' _diffrn_measurement_specimen_support 'polyimid foil' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_unetI/netI 0.0410 _diffrn_reflns_laue_measured_fraction_full 0.999 _diffrn_reflns_laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_number 45811 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.963 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.572 _diffrn_reflns_theta_min 2.129 _diffrn_source 'sealed X-Ray tube (Mo)' _diffrn_source_type 'fine focus tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.125 _exptl_absorpt_correction_T_max 0.8623 _exptl_absorpt_correction_T_min 0.7985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements (Blessing 1995) SADABS (see _computing_data_reduction) ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.426 _exptl_crystal_description block _exptl_crystal_F_000 796 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.601 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.074 _refine_ls_abs_structure_details ; Flack x determined using 2168 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.012(5) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 267 _refine_ls_number_reflns 6139 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0313 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+0.0654P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.0682 _reflns_Friedel_coverage 0.723 _reflns_friedel_fraction_full 1.000 _reflns_friedel_fraction_max 0.945 _reflns_number_gt 5551 _reflns_number_total 6139 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; ga_cr6.res created by SHELXL-2014/7 TITL ga_cr6 - #1041 - in P2(1)2(1)2(1) - superflip CELL 0.71073 5.7902 10.0948 29.8969 90 90 90 ZERR 4 0.0029 0.0045 0.0142 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N Ni O UNIT 72 104 12 4 8 L.S. 10 PLAN 25 SIZE 0.2 0.15 0.1 TEMP -173.15 BOND $H CONF MORE -1 fmap 2 acta OMIT 0 0 2 REM REM REM WGHT 0.034500 0.065400 FVAR 0.14707 NI 4 0.017757 0.314817 0.893413 11.00000 0.01271 0.00973 = 0.01272 0.00019 0.00245 -0.00098 O1 5 0.431866 0.639201 0.885518 11.00000 0.01816 0.01369 = 0.02904 -0.00142 -0.00177 -0.00414 O2 5 -0.452602 0.036950 0.930550 11.00000 0.01632 0.01944 = 0.02475 0.00328 0.00329 -0.00668 N1 3 0.238563 0.446366 0.878653 11.00000 0.01398 0.01243 = 0.01164 0.00169 -0.00007 -0.00126 N2 3 -0.138884 0.420128 0.937943 11.00000 0.01437 0.01497 = 0.01166 0.00088 -0.00033 0.00270 N3 3 -0.168948 0.162483 0.900087 11.00000 0.01279 0.01157 = 0.01556 0.00122 0.00067 -0.00099 C1 1 0.427849 0.435959 0.845690 11.00000 0.01289 0.01171 = 0.01931 0.00353 0.00206 -0.00061 H1 2 0.518237 0.364900 0.853378 11.00000 -1.20000 C2 1 0.563617 0.565113 0.852967 11.00000 0.01577 0.01977 = 0.01780 0.00473 -0.00248 -0.00526 H2A 2 0.573784 0.619278 0.825496 11.00000 -1.20000 H2B 2 0.714092 0.550910 0.865945 11.00000 -1.20000 C3 1 0.251452 0.561304 0.898498 11.00000 0.01481 0.01265 = 0.01558 0.00373 -0.00467 -0.00069 C4 1 0.101105 0.613928 0.931421 11.00000 0.02151 0.01164 = 0.01624 -0.00411 -0.00541 0.00197 H4 2 0.139897 0.694986 0.941896 11.00000 -1.20000 C5 1 -0.080552 0.546628 0.949649 11.00000 0.02110 0.01533 = 0.01069 -0.00141 -0.00395 0.00690 C6 1 -0.244278 0.600779 0.984535 11.00000 0.02657 0.02103 = 0.01457 -0.00253 0.00011 0.00866 H6A 2 -0.334647 0.675715 0.972887 11.00000 -1.20000 H6B 2 -0.157034 0.629836 1.009630 11.00000 -1.20000 C7 1 -0.401825 0.483432 0.994924 11.00000 0.01870 0.02929 = 0.01365 0.00114 0.00122 0.00949 H7A 2 -0.564959 0.506545 0.990383 11.00000 -1.20000 H7B 2 -0.387072 0.451528 1.025090 11.00000 -1.20000 C8 1 -0.323614 0.378315 0.962244 11.00000 0.01342 0.02232 = 0.00994 0.00271 -0.00069 0.00616 C9 1 -0.418697 0.254766 0.958677 11.00000 0.01250 0.02456 = 0.01684 0.00469 0.00387 0.00079 H9 2 -0.540027 0.233579 0.975910 11.00000 -1.20000 C10 1 -0.338114 0.155907 0.929164 11.00000 0.01094 0.01868 = 0.01780 0.00594 -0.00123 -0.00153 C11 1 -0.319095 -0.053045 0.903380 11.00000 0.01754 0.01627 = 0.02598 0.00376 0.00008 -0.00466 H11A 2 -0.424671 -0.106213 0.885876 11.00000 -1.20000 H11B 2 -0.214196 -0.107890 0.922923 11.00000 -1.20000 C12 1 -0.169378 0.036960 0.874252 11.00000 0.01351 0.01232 = 0.01854 0.00228 -0.00316 -0.00340 H12 2 -0.236841 0.051247 0.845687 11.00000 -1.20000 C13 1 0.068517 -0.019729 0.864402 11.00000 0.01479 0.01207 = 0.01613 -0.00096 -0.00191 -0.00110 H13 2 0.153648 -0.035963 0.892750 11.00000 -1.20000 C14 1 0.216136 0.077739 0.837964 11.00000 0.01753 0.01613 = 0.02021 -0.00188 0.00139 -0.00263 AFIX 138 H14A 2 0.363831 0.033870 0.828958 11.00000 -1.50000 H14B 2 0.251054 0.156733 0.856980 11.00000 -1.50000 H14C 2 0.130367 0.106555 0.810612 11.00000 -1.50000 AFIX 0 C15 1 0.042585 -0.150400 0.838723 11.00000 0.02667 0.01303 = 0.02218 -0.00160 -0.00400 0.00016 AFIX 138 H15A 2 -0.037909 -0.134587 0.811287 11.00000 -1.50000 H15B 2 -0.042732 -0.212196 0.856496 11.00000 -1.50000 H15C 2 0.192216 -0.185943 0.832365 11.00000 -1.50000 AFIX 0 C16 1 0.334542 0.416563 0.798077 11.00000 0.02248 0.01526 = 0.01532 -0.00159 0.00524 -0.00342 H16 2 0.226528 0.344820 0.798276 11.00000 -1.20000 C17 1 0.528971 0.385900 0.765787 11.00000 0.03295 0.04121 = 0.02660 -0.00514 0.01238 0.00384 AFIX 138 H17A 2 0.466515 0.363863 0.737519 11.00000 -1.50000 H17B 2 0.616265 0.313701 0.776771 11.00000 -1.50000 H17C 2 0.625513 0.460994 0.762913 11.00000 -1.50000 AFIX 0 C18 1 0.186086 0.531060 0.782029 11.00000 0.02528 0.02905 = 0.01670 0.00021 -0.00446 -0.00143 AFIX 138 H18A 2 0.280943 0.610616 0.779388 11.00000 -1.50000 H18B 2 0.061966 0.546817 0.803474 11.00000 -1.50000 H18C 2 0.119899 0.509365 0.752908 11.00000 -1.50000 AFIX 0 HKLF 4 REM ga_cr6 - #1041 - in P2(1)2(1)2(1) - superflip REM R1 = 0.0313 for 5551 Fo > 4sig(Fo) and 0.0390 for all 6139 data REM 267 parameters refined using 0 restraints END WGHT 0.0344 0.0691 REM Highest difference peak 0.601, deepest hole -0.315, 1-sigma level 0.074 Q1 1 -0.1208 0.3172 0.8889 11.00000 0.05 0.60 Q2 1 0.1526 0.3171 0.8953 11.00000 0.05 0.56 Q3 1 -0.0196 0.3370 0.8684 11.00000 0.05 0.54 Q4 1 0.0056 0.2505 0.8800 11.00000 0.05 0.47 Q5 1 -0.0392 0.0006 0.8709 11.00000 0.05 0.46 Q6 1 0.0596 0.2843 0.9182 11.00000 0.05 0.45 Q7 1 0.0252 0.3821 0.9036 11.00000 0.05 0.43 Q8 1 -0.2792 0.1449 0.9068 11.00000 0.05 0.39 Q9 1 -0.1677 0.1061 0.8903 11.00000 0.05 0.39 Q10 1 0.1575 0.5826 0.9120 11.00000 0.05 0.38 Q11 1 0.0686 -0.0809 0.8504 11.00000 0.05 0.37 Q12 1 0.4913 0.5025 0.8448 11.00000 0.05 0.37 Q13 1 -0.1594 0.5800 0.9646 11.00000 0.05 0.34 Q14 1 0.0356 0.2377 0.9057 11.00000 0.05 0.33 Q15 1 0.3426 0.5868 0.8932 11.00000 0.05 0.33 Q16 1 -0.0664 0.3532 0.9226 11.00000 0.05 0.33 Q17 1 0.3816 0.4319 0.8191 11.00000 0.05 0.33 Q18 1 0.0553 0.5464 0.9455 11.00000 0.05 0.32 Q19 1 -0.1075 0.4748 0.9403 11.00000 0.05 0.31 Q20 1 -0.0064 0.5742 0.9286 11.00000 0.05 0.31 Q21 1 0.0458 0.5578 0.9352 11.00000 0.05 0.31 Q22 1 -0.2320 0.3899 0.9450 11.00000 0.05 0.31 Q23 1 0.5145 0.3226 0.7772 11.00000 0.05 0.30 Q24 1 -0.3357 0.3112 0.9728 11.00000 0.05 0.29 Q25 1 0.4590 0.4089 0.7976 11.00000 0.05 0.29 ; _cod_data_source_file c5cc08950f2.cif _cod_data_source_block ga_cr6 _cod_original_cell_volume 1747.5(14) _cod_database_code 7118172 _audit_block_refno 1041 _audit_block_usercomment CR100lr_r _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.896 _shelx_estimated_absorpt_t_min 0.806 _shelxl_version_number 2014/7 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Idealised Me refined as rotating group with stretchable bonds: C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B, H18C) ; _shelx_res_checksum 35542 _olex2_submission_special_instructions 'No special instructions were received' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.01776(4) 0.31482(2) 0.89341(2) 0.01172(6) Uani 1 1 d . . . . . O1 O 0.4319(3) 0.63920(15) 0.88552(5) 0.0203(3) Uani 1 1 d . . . . . O2 O -0.4526(3) 0.03695(15) 0.93055(5) 0.0202(3) Uani 1 1 d . . . . . N1 N 0.2386(3) 0.44637(17) 0.87865(5) 0.0127(3) Uani 1 1 d . . . . . N2 N -0.1389(3) 0.42013(17) 0.93794(5) 0.0137(3) Uani 1 1 d . . . . . N3 N -0.1689(3) 0.16248(16) 0.90009(5) 0.0133(3) Uani 1 1 d . . . . . C1 C 0.4278(4) 0.4360(2) 0.84569(7) 0.0146(4) Uani 1 1 d . . . . . H1 H 0.518(4) 0.365(2) 0.8534(8) 0.018 Uiso 1 1 d R . . . . C2 C 0.5636(4) 0.5651(2) 0.85297(7) 0.0178(4) Uani 1 1 d . . . . . H2A H 0.574(4) 0.619(3) 0.8255(9) 0.021 Uiso 1 1 d R . . . . H2B H 0.714(5) 0.551(3) 0.8659(9) 0.021 Uiso 1 1 d R . . . . C3 C 0.2515(3) 0.56130(19) 0.89850(7) 0.0143(4) Uani 1 1 d . . . . . C4 C 0.1011(4) 0.6139(2) 0.93142(7) 0.0165(4) Uani 1 1 d . . . . . H4 H 0.140(5) 0.695(3) 0.9419(8) 0.020 Uiso 1 1 d R . . . . C5 C -0.0806(4) 0.5466(2) 0.94965(6) 0.0157(4) Uani 1 1 d . . . . . C6 C -0.2443(4) 0.6008(2) 0.98453(7) 0.0207(5) Uani 1 1 d . . . . . H6A H -0.335(5) 0.676(3) 0.9729(9) 0.025 Uiso 1 1 d R . . . . H6B H -0.157(5) 0.630(3) 1.0096(9) 0.025 Uiso 1 1 d R . . . . C7 C -0.4018(4) 0.4834(2) 0.99492(7) 0.0205(4) Uani 1 1 d . . . . . H7A H -0.565(5) 0.507(3) 0.9904(9) 0.025 Uiso 1 1 d R . . . . H7B H -0.387(5) 0.452(3) 1.0251(9) 0.025 Uiso 1 1 d R . . . . C8 C -0.3236(4) 0.3783(2) 0.96224(7) 0.0152(4) Uani 1 1 d . . . . . C9 C -0.4187(4) 0.2548(2) 0.95868(7) 0.0180(4) Uani 1 1 d . . . . . H9 H -0.540(5) 0.234(3) 0.9759(8) 0.022 Uiso 1 1 d R . . . . C10 C -0.3381(4) 0.1559(2) 0.92916(7) 0.0158(4) Uani 1 1 d . . . . . C11 C -0.3191(4) -0.0530(2) 0.90338(8) 0.0199(4) Uani 1 1 d . . . . . H11A H -0.425(5) -0.106(3) 0.8859(8) 0.024 Uiso 1 1 d R . . . . H11B H -0.214(5) -0.108(3) 0.9229(9) 0.024 Uiso 1 1 d R . . . . C12 C -0.1694(4) 0.0370(2) 0.87425(7) 0.0148(4) Uani 1 1 d . . . . . H12 H -0.237(4) 0.051(3) 0.8457(9) 0.018 Uiso 1 1 d R . . . . C13 C 0.0685(4) -0.0197(2) 0.86440(7) 0.0143(4) Uani 1 1 d . . . . . H13 H 0.154(4) -0.036(3) 0.8928(8) 0.017 Uiso 1 1 d R . . . . C14 C 0.2161(4) 0.0777(2) 0.83796(7) 0.0180(4) Uani 1 1 d . . . . . H14A H 0.364(3) 0.0339(8) 0.8290(5) 0.027 Uiso 1 1 calc GR . . . . H14B H 0.251(2) 0.1567(14) 0.8570(3) 0.027 Uiso 1 1 calc GR . . . . H14C H 0.1304(17) 0.1066(13) 0.8106(5) 0.027 Uiso 1 1 calc GR . . . . C15 C 0.0426(4) -0.1504(2) 0.83872(7) 0.0206(4) Uani 1 1 d . . . . . H15A H -0.038(3) -0.1346(4) 0.8113(5) 0.031 Uiso 1 1 calc GR . . . . H15B H -0.043(3) -0.2122(11) 0.8565(4) 0.031 Uiso 1 1 calc GR . . . . H15C H 0.192(2) -0.1859(10) 0.8324(5) 0.031 Uiso 1 1 calc GR . . . . C16 C 0.3345(4) 0.4166(2) 0.79808(7) 0.0177(4) Uani 1 1 d . . . . . H16 H 0.227(5) 0.345(3) 0.7983(8) 0.021 Uiso 1 1 d R . . . . C17 C 0.5290(5) 0.3859(3) 0.76579(8) 0.0336(6) Uani 1 1 d . . . . . H17A H 0.4665(12) 0.3639(19) 0.7375(5) 0.050 Uiso 1 1 calc GR . . . . H17B H 0.616(3) 0.3137(18) 0.7768(4) 0.050 Uiso 1 1 calc GR . . . . H17C H 0.626(3) 0.4610(14) 0.7629(5) 0.050 Uiso 1 1 calc GR . . . . C18 C 0.1861(4) 0.5311(2) 0.78203(7) 0.0237(5) Uani 1 1 d . . . . . H18A H 0.2809(17) 0.6106(14) 0.7794(5) 0.036 Uiso 1 1 calc GR . . . . H18B H 0.062(3) 0.5468(12) 0.8035(5) 0.036 Uiso 1 1 calc GR . . . . H18C H 0.120(3) 0.5094(8) 0.7529(5) 0.036 Uiso 1 1 calc GR . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.01271(11) 0.00973(10) 0.01272(10) 0.00019(9) 0.00245(9) -0.00098(9) O1 0.0182(7) 0.0137(6) 0.0290(8) -0.0014(6) -0.0018(6) -0.0041(6) O2 0.0163(8) 0.0194(7) 0.0247(7) 0.0033(6) 0.0033(6) -0.0067(6) N1 0.0140(8) 0.0124(7) 0.0116(7) 0.0017(6) -0.0001(6) -0.0013(6) N2 0.0144(8) 0.0150(8) 0.0117(7) 0.0009(6) -0.0003(6) 0.0027(6) N3 0.0128(7) 0.0116(7) 0.0156(8) 0.0012(6) 0.0007(6) -0.0010(6) C1 0.0129(9) 0.0117(8) 0.0193(9) 0.0035(7) 0.0021(7) -0.0006(7) C2 0.0158(10) 0.0198(10) 0.0178(9) 0.0047(8) -0.0025(7) -0.0053(8) C3 0.0148(8) 0.0126(8) 0.0156(9) 0.0037(8) -0.0047(7) -0.0007(7) C4 0.0215(10) 0.0116(9) 0.0162(9) -0.0041(7) -0.0054(8) 0.0020(8) C5 0.0211(10) 0.0153(9) 0.0107(8) -0.0014(7) -0.0040(7) 0.0069(8) C6 0.0266(12) 0.0210(11) 0.0146(9) -0.0025(8) 0.0001(9) 0.0087(9) C7 0.0187(11) 0.0293(12) 0.0136(9) 0.0011(8) 0.0012(8) 0.0095(9) C8 0.0134(9) 0.0223(10) 0.0099(8) 0.0027(7) -0.0007(7) 0.0062(8) C9 0.0125(9) 0.0246(11) 0.0168(9) 0.0047(8) 0.0039(7) 0.0008(8) C10 0.0109(9) 0.0187(10) 0.0178(9) 0.0059(7) -0.0012(7) -0.0015(7) C11 0.0175(10) 0.0163(10) 0.0260(11) 0.0038(8) 0.0001(8) -0.0047(8) C12 0.0135(9) 0.0123(9) 0.0185(9) 0.0023(7) -0.0032(8) -0.0034(7) C13 0.0148(9) 0.0121(9) 0.0161(9) -0.0010(7) -0.0019(7) -0.0011(7) C14 0.0175(10) 0.0161(10) 0.0202(10) -0.0019(8) 0.0014(8) -0.0026(8) C15 0.0267(12) 0.0130(9) 0.0222(10) -0.0016(7) -0.0040(9) 0.0002(8) C16 0.0225(11) 0.0153(10) 0.0153(9) -0.0016(7) 0.0052(8) -0.0034(8) C17 0.0329(15) 0.0412(14) 0.0266(11) -0.0051(10) 0.0124(11) 0.0038(13) C18 0.0253(12) 0.0291(12) 0.0167(10) 0.0002(9) -0.0045(9) -0.0014(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 N1 Ni N2 95.26(8) . . N3 Ni N1 168.60(7) . . N3 Ni N2 96.12(8) . . C3 O1 C2 107.31(16) . . C10 O2 C11 105.97(16) . . C1 N1 Ni 127.28(13) . . C3 N1 Ni 123.74(15) . . C3 N1 C1 108.90(17) . . C5 N2 Ni 125.12(14) . . C8 N2 Ni 124.54(15) . . C8 N2 C5 110.34(17) . . C10 N3 Ni 122.57(14) . . C10 N3 C12 107.49(17) . . C12 N3 Ni 129.84(13) . . N1 C1 H1 108.2(15) . . N1 C1 C2 102.97(16) . . N1 C1 C16 111.50(17) . . C2 C1 H1 109.6(16) . . C16 C1 H1 109.5(15) . . C16 C1 C2 114.78(17) . . O1 C2 C1 105.32(16) . . O1 C2 H2A 107.7(15) . . O1 C2 H2B 106.4(16) . . C1 C2 H2A 112.5(16) . . C1 C2 H2B 113.1(16) . . H2A C2 H2B 111(2) . . O1 C3 C4 116.87(18) . . N1 C3 O1 115.27(18) . . N1 C3 C4 127.86(19) . . C3 C4 H4 115.3(17) . . C5 C4 C3 124.32(19) . . C5 C4 H4 120.2(17) . . N2 C5 C6 111.08(19) . . C4 C5 N2 123.58(19) . . C4 C5 C6 125.34(19) . . C5 C6 H6A 111.6(15) . . C5 C6 H6B 108.8(16) . . C5 C6 C7 103.56(18) . . H6A C6 H6B 109(2) . . C7 C6 H6A 110.5(17) . . C7 C6 H6B 113.3(16) . . C6 C7 H7A 111.2(17) . . C6 C7 H7B 113.4(17) . . H7A C7 H7B 107(2) . . C8 C7 C6 103.54(18) . . C8 C7 H7A 111.4(17) . . C8 C7 H7B 110.2(17) . . N2 C8 C7 111.28(19) . . N2 C8 C9 123.92(19) . . C9 C8 C7 124.7(2) . . C8 C9 H9 119.2(17) . . C8 C9 C10 124.1(2) . . C10 C9 H9 116.7(17) . . O2 C10 C9 116.11(18) . . N3 C10 O2 115.16(18) . . N3 C10 C9 128.7(2) . . O2 C11 H11A 108.4(16) . . O2 C11 H11B 110.0(15) . . O2 C11 C12 104.50(17) . . H11A C11 H11B 113(2) . . C12 C11 H11A 112.3(16) . . C12 C11 H11B 108.4(16) . . N3 C12 C11 102.24(17) . . N3 C12 H12 109.8(16) . . N3 C12 C13 114.88(17) . . C11 C12 H12 111.7(16) . . C13 C12 C11 113.61(17) . . C13 C12 H12 104.8(16) . . C12 C13 H13 110.3(14) . . C12 C13 C14 111.44(17) . . C12 C13 C15 109.39(17) . . C14 C13 H13 105.7(15) . . C14 C13 C15 110.52(18) . . C15 C13 H13 109.5(15) . . C13 C14 H14A 109.5 . . C13 C14 H14B 109.5 . . C13 C14 H14C 109.5 . . H14A C14 H14B 109.5 . . H14A C14 H14C 109.5 . . H14B C14 H14C 109.5 . . C13 C15 H15A 109.5 . . C13 C15 H15B 109.5 . . C13 C15 H15C 109.5 . . H15A C15 H15B 109.5 . . H15A C15 H15C 109.5 . . H15B C15 H15C 109.5 . . C1 C16 H16 108.7(15) . . C17 C16 C1 110.8(2) . . C17 C16 H16 109.6(15) . . C17 C16 C18 112.0(2) . . C18 C16 C1 113.28(18) . . C18 C16 H16 102.0(16) . . C16 C17 H17A 109.5 . . C16 C17 H17B 109.5 . . C16 C17 H17C 109.5 . . H17A C17 H17B 109.5 . . H17A C17 H17C 109.5 . . H17B C17 H17C 109.5 . . C16 C18 H18A 109.5 . . C16 C18 H18B 109.5 . . C16 C18 H18C 109.5 . . H18A C18 H18B 109.5 . . H18A C18 H18C 109.5 . . H18B C18 H18C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Ni N1 1.8955(19) . Ni N2 1.9301(18) . Ni N3 1.8903(18) . O1 C2 1.445(3) . O1 C3 1.364(2) . O2 C10 1.372(3) . O2 C11 1.443(3) . N1 C1 1.478(3) . N1 C3 1.305(3) . N2 C5 1.366(3) . N2 C8 1.360(3) . N3 C10 1.311(3) . N3 C12 1.484(3) . C1 H1 0.92(2) . C1 C2 1.538(3) . C1 C16 1.535(3) . C2 H2A 0.99(3) . C2 H2B 0.96(3) . C3 C4 1.417(3) . C4 H4 0.90(3) . C4 C5 1.366(3) . C5 C6 1.512(3) . C6 H6A 0.98(3) . C6 H6B 0.95(3) . C6 C7 1.527(4) . C7 H7A 0.98(3) . C7 H7B 0.96(3) . C7 C8 1.512(3) . C8 C9 1.367(3) . C9 H9 0.90(3) . C9 C10 1.411(3) . C11 H11A 0.97(3) . C11 H11B 1.01(3) . C11 C12 1.528(3) . C12 H12 0.95(3) . C12 C13 1.520(3) . C13 H13 0.99(3) . C13 C14 1.524(3) . C13 C15 1.534(3) . C14 H14A 1.000(15) . C14 H14B 1.000(15) . C14 H14C 1.000(15) . C15 H15A 0.957(15) . C15 H15B 0.957(15) . C15 H15C 0.957(15) . C16 H16 0.96(3) . C16 C17 1.515(3) . C16 C18 1.518(3) . C17 H17A 0.946(16) . C17 H17B 0.946(16) . C17 H17C 0.946(17) . C18 H18A 0.976(16) . C18 H18B 0.976(16) . C18 H18C 0.976(16) . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Ni N1 C1 C2 -173.14(13) . . . . Ni N1 C1 C16 63.3(2) . . . . Ni N1 C3 O1 175.52(13) . . . . Ni N1 C3 C4 -4.7(3) . . . . Ni N2 C5 C4 -1.1(3) . . . . Ni N2 C5 C6 178.20(14) . . . . Ni N2 C8 C7 178.70(14) . . . . Ni N2 C8 C9 1.3(3) . . . . Ni N3 C10 O2 -178.32(13) . . . . Ni N3 C10 C9 2.4(3) . . . . Ni N3 C12 C11 167.43(14) . . . . Ni N3 C12 C13 43.9(2) . . . . O1 C3 C4 C5 -176.65(19) . . . . O2 C11 C12 N3 21.1(2) . . . . O2 C11 C12 C13 145.49(17) . . . . N1 Ni N3 C10 174.8(3) . . . . N1 Ni N3 C12 -9.2(5) . . . . N1 C1 C2 O1 -4.6(2) . . . . N1 C1 C16 C17 -171.64(19) . . . . N1 C1 C16 C18 61.5(2) . . . . N1 C3 C4 C5 3.6(3) . . . . N2 Ni N1 C1 179.17(16) . . . . N2 Ni N1 C3 2.57(17) . . . . N2 Ni N3 C10 -1.17(16) . . . . N2 Ni N3 C12 174.78(17) . . . . N2 C5 C6 C7 4.1(2) . . . . N2 C8 C9 C10 -0.5(3) . . . . N3 Ni N1 C1 3.2(5) . . . . N3 Ni N1 C3 -173.4(3) . . . . N3 C12 C13 C14 -58.9(2) . . . . N3 C12 C13 C15 178.57(16) . . . . C1 N1 C3 O1 -1.6(2) . . . . C1 N1 C3 C4 178.14(19) . . . . C2 O1 C3 N1 -1.6(2) . . . . C2 O1 C3 C4 178.61(17) . . . . C2 C1 C16 C17 71.8(2) . . . . C2 C1 C16 C18 -55.1(3) . . . . C3 O1 C2 C1 3.9(2) . . . . C3 N1 C1 C2 3.9(2) . . . . C3 N1 C1 C16 -119.71(18) . . . . C3 C4 C5 N2 -0.3(3) . . . . C3 C4 C5 C6 -179.55(19) . . . . C4 C5 C6 C7 -176.6(2) . . . . C5 N2 C8 C7 -1.2(2) . . . . C5 N2 C8 C9 -178.54(19) . . . . C5 C6 C7 C8 -4.4(2) . . . . C6 C7 C8 N2 3.6(2) . . . . C6 C7 C8 C9 -179.0(2) . . . . C7 C8 C9 C10 -177.5(2) . . . . C8 N2 C5 C4 178.74(19) . . . . C8 N2 C5 C6 -1.9(2) . . . . C8 C9 C10 O2 179.10(19) . . . . C8 C9 C10 N3 -1.6(4) . . . . C10 O2 C11 C12 -18.9(2) . . . . C10 N3 C12 C11 -16.1(2) . . . . C10 N3 C12 C13 -139.67(18) . . . . C11 O2 C10 N3 9.5(2) . . . . C11 O2 C10 C9 -171.12(18) . . . . C11 C12 C13 C14 -176.16(18) . . . . C11 C12 C13 C15 61.3(2) . . . . C12 N3 C10 O2 4.9(2) . . . . C12 N3 C10 C9 -174.4(2) . . . . C16 C1 C2 O1 116.74(19) . . . .